Methyl 3-formylbenzoate → Methyl 3-[2(E)-(quinolin-2-yl)ethenyl]benzoate

HRID 54527ノート

反応式

HRID 54527 の反応式
C([Li])CCC.[Cl-].[N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[CH2:17][PH3+].[CH:19]([C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=1)[C:24]([O:26][CH3:27])=[O:25])=O>CCCCCC.O1CCCC1.O>[N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1/[CH:17]=[CH:19]/[C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=1)[C:24]([O:26][CH3:27])=[O:25]

参加物

7

反応物 3

HCID 639145Methyl 3-formylbenzoateHCID 19959097Quinolin-2-ylmethylphosphonium chlorideHCID 178418339Butyllithium

生成物 1

HCID 19959111Methyl 3-[2(E)-(quinolin-2-yl)ethenyl]benzoate

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-75 °C

実験手順

2.5M Butyl lithium in hexane (8.8 ml) is added over 5 minutes to a stirred solution of quinolin-2-ylmethylphosphonium chloride (9.66 g, 22 mmol) in dry tetrahydrofuran (250 ml) at -75° C. The mixture is stirred for 1 hour at -75° C. then a solution of methyl 3-formylbenzoate (3.28 g, 20 mmol) in tetrahydrofuran (25 ml) is added dropwise over 10 minutes. After stirring for a further 30 minutes at -75° C., the mixture is warmed to room temperature, diluted with water and extracted with ethyl acetate. The extract is dried and evaporated and the residue is purified by chromatography on silica eluting with ethyl acetate-hexane (1:3).

後処理

  1. stirringAfter stirring for a further 30 minutes at -75° C.
  2. temperaturethe mixture is warmed to room temperature
  3. extractionextracted with ethyl acetate
  4. customThe extract is dried
  5. customevaporated
  6. customthe residue is purified by chromatography on silica eluting with ethyl acetate-hexane (1:3)

出典と根拠

ORDレコード
ord-4e243abca980471d981fb852570dde9a
出典データセット
uspto-grants-1997_04
特許番号
US05622969

反応ノート

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